197143-14-9

Upstream product

• 84094-74-6 (1S,3R)-(-)-methyl 2-benzyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate 
• 4220-66-0 methyl 4,4-dimethoxybutanoate 
• 13865-19-5 4-oxobutanoic acid methyl ester 
• 4299-70-1 D-Tryptophan methyl ester 
• 100-52-7 benzaldehyde 
• 84094-75-7 cis-(1R,3R)-(+)-2-benzyl-3-(methoxycarbonyl)-1-<(methoxycarbonyl)ethyl>-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole 
• 63229-68-5 D-(+)-N_bbenzyltryptophan methyl ester 

Downstream Products

• 197143-13-8 (6S,10S)-(-)-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cycloocta[b]indole 
• 217448-24-3 (6S,10S)-(-)-9-formyl-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctaindole 
• 217448-25-4 (6S,10S)-9-(1'-hydroxy-3'-hexenyl)-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctaindole 
• 123806-87-1 (6S,10S)-(-)-5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole 

Relevant academic research and scientific papers

Enantiospecific Total Synthesis of the Sarpagine Related Indole Alkaloids Talpinine and Talcarpine as Well as the Improved Total Synthesis of Alstonerine and Anhydromacrosalhine-methine via the Asymmetric Pictet-Spengler Reaction

The enantiospecific total synthesis of talpinine 1 and talcarpine 2 has been accomplished from D-(+)-tryptophan in 13 steps (11 reaction vessels) in 10% and 9.5% overall yields, respectively. Moreover, this synthetic approach has been employed for the improved synthesis of alstonerine 3 and anhydromacrosalhine-methine 4 in 12% and 14% overall yield, respectively. A convenient synthetic route for the enantiospecific, stereospecific preparation of the key intermediate (-)-Na-H, Nb-benzyl tetracyclic ketone 15a via the asymmetric Pictet-Spengler reaction on a multihundredgram scale has been developed. A diastereocontrolled (>30:1) anionic oxy-Cope rearrangement and the intramolecular rearrangement to form ring-E and an Nb-benzyl/Nb-methyl transfer reaction also served as key steps. This general approach can now be utilized for the synthesis of macroline/ sarpagine related indole alkaloids and their antipodes for biological screening.

General approach for the synthesis of macroline/sarpagine related indole alkaloids via the asymmetric Pictet-Spengler reaction: The enantiospecific synthesis of the N(a)-H, azabicyclo[3.3.1]nonone template

N(a)-H, N(b)-benzyltetracyclic ketone 1a, a potential intermediate for the synthesis of numerous sarpagine-related alkaloids, has been synthesized enantiospecifically from D-(+)-tryptophan via the asymmetric Pictet-Spengler reaction.